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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2170307Generated: October 25, 2026

Diisobutylaluminumhydride → N-(5-Bromo-6-formyl-2-pyridinyl)acetamide

https://huagongshe.com/reaction/2170307

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisobutylaluminumhydrideHCID 21225700—
Reactant6-acetamido-3-bromo-N-methoxy-N-methylpicolinamideHCID 90280477—
SolventTetrahydrofuranHCID 8028—
ProductN-(5-Bromo-6-formyl-2-pyridinyl)acetamideHCID 90280237—

Reaction Steps

To the crude material from last step (1B, 2.6 g, 8.6 mmol) in THF (tetrahydrofuran)(30 mL) was added DIBAL-H (diisobutylaluminium hydride)(13 mmol, 1.5 equiv) dropwise at 70° C. The reaction was stirred for 1 h and was then quenched with NH4Cl solution. The reaction mixture was partitioned between EtOAc and saturated NH4Cl solution. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was used in the next step without further purification. MS (m/z) 244.1 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09050344B2
Source datasetuspto-grants-2015_06
ORD IDord-2eb5869b1a384c52a45f79d471c447f1
Source noteuspto-grants-2015_06